1. Field of the Invention
This invention relates to certain mono- and disubstituted hydroxyguanidines including selected phenyl-and benzylhydroxyguanidines, and their use as metal chelating agents and as antidepressants.
2. Prior Art
J. V. Braun and R. Schwarz, Ber., 36, 3660 (1903) describe the preparation of the hydroxyguanidines, ##EQU1## where R.sup.1 = C.sub.6 H.sub.5, R.sup.2 = CH.sub.3 ; R.sup.1 = R.sup.2 = n-propyl; and R.sup.1 = R.sup.2 = C.sub.6 H.sub.5.
In a series of papers, Belzecki and coworkers described the preparation and properties of several types of 1,1- and 1,3-disubstituted hydroxyguanidines but no examples of benzyl-substituted compounds were mentioned (C. Belzecki et al., Bull. Acad. Pol. Sci., Ser. Sci. Chim., 19 (6-7), 367 (1971); ibid, 18 (8), 431 (1970); ibid, 18 (7), 375, 379 (1970); J. Chem. Soc. D, 806 (1970) ). U.S. Pat. No. 3,505,336 discloses hydroxyguanidines of the type ##SPC1##
And their diacetyl derivatives as antihypertensive agents.
Certain monoalkyl-substituted hydroxyguanidine-O-sulfonic acid salts have been described (Hessing and Peppmoller, Z. Naturforsch., 22, 820 (1967) ), and 1,3-dialkylhydroxyguanidines have been prepared from 1,3-dialkylsubstituted carbodiimides (Zinner and Gross, Chem. Ber., 105, 1709 (1972) ).
Certain 1-hydroxy-2-phenylguanidines, ##SPC2##
And their use as herbicides have been described (Ger. Offen. 2,040,628, Feb. 24, 1972).